Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate → 5-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

HRID 1034260노트

반응식

HRID 1034260 반응식
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:21])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:22][C:23](OCC)=[O:24])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:21])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:22][CH2:23][OH:24])=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 19023676Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 190236775-(4-Chlorobenzyl)-4-(2-hydroxyethyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of product from Step 3 (785 mg, 1.83 mmol) in THF (30 mL), cooled to 0° C. and under N2 atmosphere, there was added LiAlH4 (152 mg, 4 mmol). The resulting mixture was stirred at 0° C. for 30 minutes, then quenched carefully with ice-cold H2O, and acidified with 1N aq HCl (10 mL). The mixture was extracted twice with Et2O, and these extracts were washed 3× with brine, dried over Na2SO4, and evaporated. The residue was chromatographed, eluting with a 1:1 mixture of EtOAc and hexane, to afford the title product as a thick oil.

후처리

  1. customquenched carefully with ice-cold H2O
  2. extractionThe mixture was extracted twice with Et2O
  3. washthese extracts were washed 3× with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was chromatographed
  7. washeluting with a 1:1 mixture of EtOAc and hexane

출처 및 근거

ORD 기록
ord-a47bbad0e9c04504893f39c3cb589083
출처 데이터셋
uspto-grants-1994_05
특허 번호
US05314898

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